The present invention relates to the use of 3,5-dihydroxystilbene or 3-hydroxystilbene and/or derivatives thereof as deodorant active agents in the preparation of a cosmetic composition, to the deodorant cosmetic composition containing these compounds and to the use of the composition for human topical application. The invention also relates to a process for treating human underarm odors, which comprises applying an effective amount of the composition to the armpit area.
In the cosmetics field, it is a well-known practice to use, in topical application, deodorant products containing active substances of antiperspirant type or of bactericidal type to reduce or even eliminate underarm odors, which are generally unpleasant. Antiperspirants have the effect of limiting the flow of sweat. They generally consist of aluminium salts, which, on the one hand, are skin irritants and, on the other hand, reduce the flow of sweat by modifying the skin physiology, which is unsatisfactory. Bactericides inhibit the growth of the skin flora responsible for underarm odors. Among bactericidal products, the one most commonly used is Triclosan (2,4,4xe2x80x2-trichloro-2xe2x80x2-hydroxydiphenyl ether), which has the drawback of considerably modifying the ecology of the skin flora and of being inhibited by certain compounds such as, for example, nonionic surfactants, commonly used in the formulation of cosmetic compositions. Moreover, the insoluble nature of Triclosan in water does not allow it to be incorporated into essentially aqueous formulations.
With the aim of obtaining long-term efficacy, novel products are sought that exert a deodorant action, i.e., products capable of modifying, reducing and/or eliminating or preventing the development of body odor (this definition is given in the book xe2x80x9cCosmetic Science and Technology Seriesxe2x80x9dxe2x80x941988/Volume 7, chapter 10-IIIc, incorporated by reference herein). In addition, products are sought that do not have the drawbacks of the active substances used in the prior art. It is known that certain stilbene compounds, such as 4-hydroxystilbene and 3,5,4xe2x80x2-stilbene (or Resveratrol), make it possible to limit the development of sweat odor. However, the efficacy of these molecules is very markedly insufficient.
After considerable research conducted in this matter, the inventors have now discovered, surprisingly and unexpectedly, that the compounds of formula (I) defined below have the property of preventing the development of body odor, without the drawbacks of the active substances previously used in deodorant compositions, and with the advantage, for some of these compounds, of being water-soluble in proportions that are advantageous and sufficient to be easy to place in formulation, especially in water-based cosmetic compositions for human topical application. This discovery forms the basis of the present invention.
A first subject of the present invention is thus the use of compounds of formula (I) below as deodorant active agents in cosmetic compositions: 
in which:
A denotes a hydrogen atom or a radical OR2,
R1 and R2, which may be identical or different, denote a hydrogen atom; a C1-C4 alkyl radical; an acyl radical R3CO in which R3 denotes a linear or branched, saturated or unsaturated, hydroxylated or non-hydroxylated, carboxylated or non-carboxylated C1-C30 hydrocarbon-based radical; a radical PO(OX1)(OX2) or a radical SO2(OX3) in which X1, X2 and X3, which may be identical or different, denote a hydrogen atom or a monovalent alkali metal or NH4+ cation, in which X1 and/or X2 can also denote a divalent metal cation; a glycosyl radical; or a uronyl radical; and
R4 and R5, which are identical, denote a hydrogen atom or a hydroxyl radical.
A second subject of the invention is a deodorant cosmetic composition comprising at least one compound of formula (I) described above. Another subject of the invention is the use of the composition in or for the manufacture of deodorant cosmetic products intended for human topical application. Yet another subject of the invention is the use of at least one compound of formula (I) described above, as a selective inhibitor of certain bacterial species constituting the human skin flora, and, in particular, Corynebacterium xerosis. Still another subject of the invention is a process for treating human underarm odors, which comprises applying an effective amount of the composition to the armpit area.
A subject of the invention is also novel compounds of formula (I) as defined above, in which A denotes a hydrogen atom or a radical OR2, R1 and R2, which may be identical or different, denote an acyl radical R3CO in which R3 denotes a linear or branched, saturated or unsaturated, hydroxylated or non-hydroxylated, carboxylated or non-carboxylated C4-C30 hydrocarbon-based radical; a radical PO(OX1)(OX2) or a radical SO2(OX3) in which X1, X2 and X3, which may be identical or different, denote a hydrogen atom or a monovalent alkali metal or NH4+ cation, in which X1 and/or X2 can also denote a divalent metal cation; or a uronyl radical, and R4 and R5, which are identical, denote a hydrogen atom or a hydroxy radical.
Another subject of the invention is a cosmetic composition comprising at least one compound of formula (I) defined above, in which A denotes a hydrogen atom or a radical OR2, R1 and R2, which may be identical or different, denote an acyl radical R3CO in which R3 denotes a linear or branched, saturated or unsaturated, hydroxylated or non-hydroxylated, carboxylated or non-carboxylated C1-C30 hydrocarbon-based radical; a radical PO(OX1)(OX2) or a radical SO2(OX3) in which X1, X2 and X3, which may be identical or different, denote a hydrogen atom or a monovalent alkali metal or NH4+ cation, in which X1 and/or X2 can also denote a divalent metal cation; or a uronyl radical, and R4 and R5, which are identical, denote a hydrogen atom or a hydroxyl radical.
In formula (I) described above, the alkyl radicals can be linear or branched and, in particular, denote methyl, ethyl, propyl, isopropyl, n-propyl, butyl, n-butyl or tert-butyl radicals. Preferably, the alkyl radical denotes a methyl radical and the glycosyl radical denotes a saccharose or saccharide radical, such as arabinose, glucose, fructose or sucrose. More preferably, the glycosyl radical denotes a glucosyl radical; also preferably the uronyl radical denotes a mannuronyl or glucuronyl radical.
Among the compounds of formula (I) used according to the present invention, particular examples include 3,5-dihydroxystilbene (or Pinosylvine), its monomethyl and dimethyl ethers, 3,5,3xe2x80x2,4xe2x80x2-tetrahydroxystilbene, and the corresponding mono- and diglycoside forms. Mention may also be made of 3-hydroxystilbene and its methyl ether.
In the present invention, the glucoside and glucuronide forms of these compounds of formula (I) are particularly advantageous since, on account of their water-solubility, they have the advantage of being easy to place in formulation in essentially an aqueous medium. In addition, they can release the active substance in situ under the action of glycosidases of bacterial origin, which are present under the armpits.
According to the invention, it is even more particularly preferred to use 3,5-dihydroxystilbene (or Pinosylvine), which, in comparison with Triclosan that is well known in the field under consideration, has the advantage of being more effective regarding deodorant activity, of being odorless at working concentrations, and of being more respectful to the skin""s bacterial flora, since its bactericidal action is selective on Corynebacterium xerosis, the main strain producing perspiration odors.
The compounds of formula (I) according to the invention preferably represent 0.001 to 10% by weight approximately relative to the total weight of the deodorant cosmetic composition, more particularly, from 0.01 to 5%, and, even more particularly, from 0.1 to 5% by weight approximately relative to this weight.
The compounds of formula (I) described above, in which A denotes a hydrogen atom or a radical OR2, and R1 and R2, which may be identical or different, denote a hydrogen atom; a C1-C4 alkyl radical or a glycosyl radical, are in natural form, especially in the plants of the genera:
Pinus, and, in particular, Pinus montana mill., Pinus sylvestris L, Pinus contorta var. Latifolia S. Wats, Pinus ponderosa Dougl., Pinus Halpensis Mill. from the Pinacea family;
Alnus, and, in particular, Alnus sieboldiana from the Betulacea family;
Polygonum, and, in particular, Polygonum nodosum from the Polygonacea family;
Dalbergia, and, in particular, Dalbergia sissoo from the Leguminosa family;
Scutellaria, and, in particular, Scutellaria scandens from the Lamiacea family;
Lindera, and, in particular, Lindera reflexa from the Lauracea family.
3,5-dihydroxystilbene and its monomethyl and dimethyl ethers can be extracted from the wood of plants of the genus Pinus; 3,5-dihydroxystilbene monoglucoside can be extracted from the roots of plants of the genus Scutellaria; 3,5-dihydroxystilbene diglucoside can be extracted from plants of the genus Lindera. 3,5,3xe2x80x2,4xe2x80x2-Tetrahydroxystilbene (or Piceatannol or Astringenin) can be extracted from the wood of pine and spruce trees and from a leguminous plant (Laburnum anagyroides). 3,5-Dihydroxystilbene, 3-hydroxystilbene and 3,5,3xe2x80x2,4xe2x80x2-tetrahydroxystilbene can be derived from plant extracts, as described above, and can be obtained by any extraction method known to those skilled in the art or can be obtained by synthesis according to methods that are generally well known in the literature. Particular examples include alcoholic extracts, especially ethanolic extracts, and aqueous-alcoholic extracts.
The deodorant cosmetic composition according to the invention can comprise, in addition to the compound(s) of formula (I) according to the invention, other deodorant or antiperspirant active agents conventionally used in this type of composition. For the purposes of the present invention, the expression xe2x80x9cdeodorant active agentxe2x80x9d means any substance capable of reducing the flow of sweat and/or of masking, improving or reducing the unpleasant odor resulting from the decomposition of human sweat by bacteria. These deodorant active agents can be chosen, for example, from: water-soluble zinc salts such as, for example, zinc pyrrolidonecarboxylate (more particularly known as zinc pidolate), zinc sulphate, zinc chloride, zinc lactate, zinc gluconate and zinc phenolsulphonate; antiperspirant active agents, for instance aluminium salts such as, for example, aluminium chloride or aluminium hydroxyhalides, zirconium salts such as, for example, zirconium oxide salts or hydroxyzirconyl salts, metal complexes such as aluminium or zirconium with an amino acid such as, for example, glycine, as described in U.S. Pat. No. 3,792,068, incorporated herein by reference; bactericides such as 2,4,4xe2x80x2-trichloro-2xe2x80x2-hydroxydiphenyl ether (Triclosan) and 3,7,11-trimethyidodeca-2,5,10-trienol (Farnesol). These additional deodorant active agents can be present in the composition according to the invention in a proportion from about 0.001 to 20% by weight relative to the total composition, and, preferably, in a proportion from about 0.1 to 10% by weight.
The deodorant cosmetic composition according to the invention is conventionally formulated depending on the presentation form for which it is intended. It is preferably formulated in a cosmetically acceptable vehicle that may, in particular, be essentially aqueous, or may contain organic solvents and especially C1-C4 monoalcohols, preferably ethanol, to accelerate the evaporation of the product, or propylene glycol, dipropylene glycol or ethers thereof. The deodorant cosmetic composition according to the invention can also be formulated as a water-in-oil or oil-in-water emulsion or as a water-in-oil-in-water triple emulsion (such emulsions are known and described, for example, by C. Fox in xe2x80x9cCosmetics and Toiletriesxe2x80x9dxe2x80x94November 1986xe2x80x94Vol 101xe2x80x94pages 101-112, incorporated herein by reference).
The deodorant cosmetic composition of the invention can also comprise cosmetic adjuvants chosen from fatty substances, gelling agents, emollients, softeners, antioxidants, opacifiers, stabilizers, anti-foaming agents, moisturizers, vitamins, fragrances, preserving agents, surfactants, fillers, sequestering agents, polymers, propellants, acidifying or basifying agents, dyes, pigments, thickeners or any other ingredient usually used in cosmetics for this type of application. If surfactants are used, they are preferably chosen from anionic, amphoteric or nonionic surfactants. Needless to say, a person skilled in the art will take care to select this or these optionally additional compound(s) such that the advantageous properties intrinsically associated with the deodorant cosmetic composition according to the invention are not, or are not substantially, adversely affected by the addition(s) envisaged.
Fatty substances useful in the present invention can comprise an oil or a wax or a mixture thereof, petroleum jelly, paraffin, lanolin, hydrogenated lanolin or acetylated lanolin; they also comprise fatty acids, fatty alcohols such as lauryl alcohol, cetyl alcohol, myristyl alcohol, stearyl alcohol, palmityl alcohol, oleyl alcohol or 2-octyldodecanol, fatty acid esters such as glyceryl monostearate, polyethylene glycol monostearate, isopropyl myristate, isopropyl adipate, isopropyl palmitate, octyl palmitate, C12-C15 fatty alkyl benzoates (Finsolv TN from Finetex), myristyl alcohol polyoxypropylenated with 3 mol of propylene oxide (Witconol APM from Witco), C6-C8 fatty acid triglycerides such as caprylic/capric acid triglycerides.
When the fatty substances comprise or include oils, the oils are chosen from animal, plant, mineral and synthetic oils and, in particular, hydrogenated palm oil, hydrogenated castor oil, liquid petroleum jelly, liquid paraffin, purcellin oil (stearyl octanoate), silicone oils and isoparaffins. When the fatty substances comprise or include waxes, the waxes are chosen from animal, fossil, plant, mineral and synthetic waxes. Particular examples include beeswaxes, carnauba wax, candelilla wax, sugarcane wax, Japan wax, ozokerites, montan wax, microcrystalline waxes, paraffins and silicone waxes and resins.
Thickeners useful in the present invention, which are preferably nonionic, can be chosen from modified or unmodified guar gums and celluloses, such as hydroxypropyl guar gum, cetylhydroxyethylcellulose, silicas such as, for example, Bentone Gel MiO sold by the company NL Industries or Veegum Ultra sold by the company Polyplastic.
The deodorant cosmetic composition can comprise emollients, which contribute towards a soft, dry, non-sticky sensation when the composition is applied to the skin. These emollients can be chosen from products such as volatile silicones, non-volatile silicones and other non-volatile emollients.
The volatile silicones are defined, in a known manner, as compounds that are volatile at room temperature. Among these compounds, mention may be made of cyclic, linear volatile silicones of the dimethylsiloxane type whose chains comprise from 3 to 9 silicone residues. Cyclomethicone D4 or D5 is preferably chosen.
The non-volatile silicones are defined, in a known manner, as compounds with a low vapour pressure at room temperature. Among these compounds are included: polyalkylsiloxanes, in particular, linear polyalkylsiloxanes such as, for example, polydimethylsiloxanes, or linear dimethicones, sold by the company Dow Corning under the name xe2x80x9cDow Corning 200 Fluidxe2x80x9d; polyalkylarylsiloxanes such as, for example, the polymethylphenylsiloxanes sold by the company Dow Corning under the name xe2x80x9cDow Corning 556 Fluidxe2x80x9d; polyether and siloxane copolymers such as, for example, dimethicone copolyols.
Among the non-volatile emollients that can be used in the present invention, examples include: hydrocarbon-based derivatives, mineral oils, fatty alcohols, esters of C3-C18 alcohols with C3-C18 acids, esters of benzoic acid with C12-C18 alcohols and mixtures thereof, C2-C6 polyols preferably chosen from glycerol, propylene glycol and sorbitol, and polyalkylene glycol polymers.
The amounts of these various constituents that may be present in the deodorant cosmetic composition according to the invention are those which are conventionally used for the presentation forms under consideration.
The deodorant composition according to the invention can be in the form of a lotion, a cream or a fluid gel distributed as an aerosol spray, in a pump-dispenser bottle or as a roll-on, in the form of a thickened cream distributed in a tube and in the form of a stick or powder, and, in this respect, can contain the ingredients and propellants generally used in products of this type and which are well known to those skilled in the art.
The present invention is further illustrated by the following examples which are designed to teach those of ordinary skill in the art how to practice the invention. The following examples are merely illustrative of the invention and should not be construed as limiting the invention as claimed.